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Sailing Trips Starting In October 2026 and 2027

Are you looking to embark on a sailing trip in October 2026 or 2027? Choose from 32 unique trip itineraries and 710 departures from the world's leading touring operators.
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32 Trips (710 Departures)
32 Trips (710 Departures)
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6 Days
26 Days
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$22,449pp
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8 Day Croatia Sailing Adventure: Dubrovnik to Split with Intrepid Travel
Cruise
 (1)

8 Days (7 Nights) Dubrovnik to Split
Operator: Intrepid
Departures: Sep 2026 to Oct 2026
Visits: Croatia
Exclusive Savings
From (Per Person)
A$2,138
Save 908
Per Person
View Trip
14 Day Essential India & Maldives Sailing with G Adventures
Tour + Cruise

14 Days Delhi to Male
Operator: G Adventures
Departures: Sep 2026 to Dec 2027
Trip Styles: Adventure, Small Group, Sailing
Visits: India, Maldives
Exclusive Savings
From (Per Person)
A$3,370
Save 1,075
Per Person
View Trip
7 Day Maldives Cruise: Indian Ocean Dhoni Life with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operator: G Adventures
Departures: Oct 2026 to Jan 2028
Visits: Maldives
Exclusive Savings
From (Per Person)
A$2,057
Save 880
Per Person
View Trip
18 Day Sri Lanka with Maldives Cruise: Spice Gardens & Seasides with G Adventures
Tour + Cruise

18 Days Negombo to Male
Operator: G Adventures
Departures: Oct 2026 to Dec 2027
Trip Styles: Small Group, 18-30's, Sailing
Visits: Sri Lanka, Maldives
Exclusive Savings
From (Per Person)
A$3,762
Save 1,362
Per Person
View Trip
18 Day Bali & Beyond with TruTravels
New ReleaseTour + Cruise

18 Days Canggu to Labuan Bajo
Operator: TruTravels
Departures: Oct 2026 to Nov 2027
Trip Styles: Adventure, Small Group, 18-30's, Island Hopping, Sailing
Visits: Indonesia
Exclusive Savings
From (Per Person)
A$2,252
Save 843
Per Person
View Trip
10 Day Egypt: Pyramids, Temples & the Nile with G Adventures
New ReleaseTour + River Cruise

10 Days Cairo to Cairo
Operator: G Adventures
Departures: Sep 2026 to Dec 2027
Rivers: Nile
Visits: Egypt
Exclusive Savings
From (Per Person)
A$7,202
Save 176
Per Person
View Trip
7 Day Sailing the Canary Islands with G Adventures
Cruise

7 Days (6 Nights) San Miguel de Abona to San Miguel de Abona
Operator: G Adventures
Departures: Oct 2026 to Apr 2028
Visits: Spain
Exclusive Savings
From (Per Person)
A$1,410
Save 421
Per Person
View Trip
8 Day Greece Sailing Adventure: Corfu to Kefalonia with Intrepid Travel
Cruise

8 Days (7 Nights) Corfu to Kefalonia
Operator: Intrepid
Departures: Sep 2026 to Oct 2026
Visits: Greece
Exclusive Savings
From (Per Person)
A$3,550
Save 456
Per Person
View Trip
9 Day Komodo Island Hopper with TruTravels
New ReleaseTour + Cruise

9 Days Lombok to Labuan Bajo
Operator: TruTravels
Departures: Sep 2026 to Nov 2027
Trip Styles: Adventure, Small Group, 18-30's, Island Hopping, Sailing
Visits: Indonesia
Exclusive Savings
From (Per Person)
A$1,419
Save 531
Per Person
View Trip
7 Day Amalfi Coast Sailing Adventure with Intrepid Travel
Cruise

7 Days (6 Nights) Naples to Procida
Operator: Intrepid
Departures: Aug 2026 to Oct 2027
Visits: Italy
Exclusive Savings
From (Per Person)
A$3,284
Save 1,135
Per Person
View Trip
8 Day Montenegro Sailing with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Dubrovnik
Operator: G Adventures
Departures: Aug 2026 to Oct 2027
Visits: Montenegro, Croatia
Exclusive Savings
From (Per Person)
A$2,132
Save 587
Per Person
View Trip
8 Day Sail Maldives with Intrepid Travel
Cruise

8 Days (7 Nights) Male to Male
Operator: Intrepid
Departures: Sep 2026 to Dec 2027
Visits: Maldives
Exclusive Savings
From (Per Person)
A$3,328
Save 1,010
Per Person
View Trip
26 Day Total Indonesia with TruTravels
New ReleaseTour + Cruise

26 Days Medan to Labuan Bajo
Operator: TruTravels
Departures: Oct 2026 to Oct 2027
Trip Styles: Adventure, Small Group, 18-30's, Island Hopping, Sailing
Visits: Indonesia
Exclusive Savings
From (Per Person)
A$4,710
Save 685
Per Person
View Trip
8 Day Sailing Greece - Santorini to Mykonos with G Adventures
Cruise

8 Days (7 Nights) Santorini to Mykonos
Operator: G Adventures
Departures: Aug 2026 to Oct 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$1,763
Save 636
Per Person
View Trip
8 Day Sailing Greece - Mykonos to Athens with G Adventures
Cruise

8 Days (7 Nights) Mykonos to Athens
Operator: G Adventures
Departures: Aug 2026 to Oct 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$1,496
Save 853
Per Person
View Trip
6 Day Komodo & Flores Sail with Contiki
New ReleaseTour + Cruise

6 Days Sanur to Labuan Bajo
Operator: Contiki
Departure: 24 October 2026
Trip Styles: Small Group, 18-30's, Island Hopping, Sailing, Short Break, Scenic
Visits: Indonesia
Exclusive Savings
From (Per Person)
A$2,128
Save 38
Per Person
View Trip
8 Day Croatia Sailing Adventure: Split to Dubrovnik with Intrepid Travel
Cruise

8 Days (7 Nights) Split to Dubrovnik
Operator: Intrepid
Departures: Aug 2026 to Oct 2027
Visits: Croatia
Exclusive Savings
From (Per Person)
A$2,138
Save 908
Per Person
View Trip
22 Day Sri Lanka in Depth with Maldive Dhoni Cruise (Horton Plains) with Explore Worldwide
Tour + Cruise

22 Days Negombo to Male
Operator: Explore
Departures: Jul 2027 to Nov 2027
Trip Styles: Adventure, Sailing
Visits: Sri Lanka, Maldives
Exclusive Savings
From (Per Person)
A$7,699
Save 634
Per Person
View Trip
8 Day Turkey: Sail & Swim with Topdeck
New ReleaseCruise

8 Days (7 Nights) Fethiye to Fethiye
Operator: Topdeck
Departures: Sep 2026 to Oct 2026
Visits: Turkey
Exclusive Savings
From (Per Person)
A$1,768
Save 131
Per Person
View Trip
8 Day Sail Greece: Mykonos to Santorini with Intrepid Travel
Cruise

8 Days (7 Nights) Mykonos to Santorini
Operator: Intrepid
Departures: Aug 2026 to Oct 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,456
Save 635
Per Person
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operator: G Adventures
Departures: Aug 2026 to Oct 2027
Visits: Croatia
Exclusive Savings
From (Per Person)
A$1,865
Save 854
Per Person
View Trip
7 Day Maldives Dhoni Cruise with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operator: G Adventures
Departures: Sep 2026 to Dec 2027
Visits: Maldives
Exclusive Savings
From (Per Person)
A$2,057
Save 880
Per Person
View Trip
8 Day Montenegro Sailing Adventure from Dubrovnik with Intrepid Travel
Cruise

8 Days (7 Nights) Dubrovnik to Dubrovnik
Operator: Intrepid
Departures: Sep 2026 to Oct 2027
Visits: Croatia, Montenegro
Exclusive Savings
From (Per Person)
A$2,279
Save 767
Per Person
View Trip
14 Day Highlights of Sri Lanka with Maldive Dhoni Cruise (East Coast) with Explore Worldwide
Tour + Cruise

14 Days Negombo to Male
Operator: Explore
Departures: Aug 2027 to Oct 2027
Trip Styles: Adventure, Small Group, Sailing
Visits: Maldives, Sri Lanka
Exclusive Savings
From (Per Person)
A$5,493
Save 415
Per Person
View Trip
17 Day Signature: Egypt & Jordan's Ancient Wonders with G Adventures
New ReleaseTour + River Cruise

17 Days Cairo to Dead Sea
Operator: G Adventures
Departures: Mar 2027 to Mar 2028
Rivers: Nile
Visits: Egypt, Jordan
Exclusive Savings
From (Per Person)
A$19,893
Save 449
Per Person
View Trip
14 Day Sri Lanka & Maldives Adventure with G Adventures
Tour + Cruise

14 Days Negombo to Male
Operator: G Adventures
Departures: Oct 2026 to Dec 2027
Trip Styles: Adventure, Small Group, Island Hopping, Sailing
Visits: Sri Lanka, Maldives
Exclusive Savings
From (Per Person)
A$4,497
Save 1,335
Per Person
View Trip
8 Day Maldive Dhoni Cruise with Explore Worldwide
Cruise

8 Days (7 Nights) Male to Male
Operator: Explore
Departures: Aug 2026 to Dec 2027
Visits: Maldives
Exclusive Savings
From (Per Person)
A$2,911
Save 340
Per Person
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Split to Dubrovnik
Operator: G Adventures
Departures: Aug 2026 to Oct 2027
Visits: Croatia
Exclusive Savings
From (Per Person)
A$1,769
Save 810
Per Person
View Trip
7 Day Egypt: Ancient Wonders & Temples of the Nile with G Adventures
New ReleaseTour

7 Days Cairo to Luxor
Operator: G Adventures
Departures: Sep 2026 to Jan 2028
Trip Styles: Adventure, Small Group, Sailing
Visits: Egypt
Exclusive Savings
From (Per Person)
A$3,966
Save 1,093
Per Person
View Trip
7 Day Maldives Dhoni Explorer with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operator: G Adventures
Departures: Sep 2026 to Dec 2027
Visits: Maldives
Exclusive Savings
From (Per Person)
A$2,195
Save 1,033
Per Person
View Trip
Results: 1-30 of 32

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